2-ethoxy-4-formyl phenyl ester of propionic acid and use in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles

ABSTRACT

Described is 2-ethoxy-4-formyl phenyl ester of propionic acid of our invention defined according to the structure:   &lt;IMAGE&gt;   and uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes.

BACKGROUND OF THE INVENTION

The present invention relates to 2-ethoxy-4-formyl phenyl ester ofpropionic acid of our invention defined according to the structure:##STR2## and uses thereof in augmenting or enhancing the aroma ofperfume compositions, colognes and perfumed articles (including solid orliquid anionic, cationic, nonionic or zwitterionic detergents, fabricsoftener compositions and fabric softener articles, cosmetic powders,hair preparations and perfumed polymers).

There has been considerable work performed relating to substances whichcan be used to impart (augment or enhance) fragrances (to) or (in)various consumable materials. These substances are used to diminish theuse of natural materials some of which may be in short supply and toprovide more uniform properties in the finished product. In addition,there is a need to use in such consumable materials perfume materialswhich are non-discoloring.

Rich, natural vanilla bean and sweet aromas with dark chocolate topnotesare highly desirable for many uses in perfume compositions, perfumedarticles and colognes particularly where a "sweet" note is needed to beadded to musk formulations and citrusy formulations.

Esters of various vanilla derivatives are known in the prior art andfurthermore are known to be useful in flavors and fragrances. Thus,vanillin acetate having the structure: ##STR3## is described byNunomura, et al in Agric. Biol. Chem. 44 (2), 39-351 (at page 345) to bea flavor component in the acetic fraction of Shoyu (soy sauce).Furthermore, the vanillin acetate having the structure: ##STR4## andvanillin isobutyrate having the structure: ##STR5## as well as ethylvanillin acetate having the structure: ##STR6## are disclosed in "FlavorAnd Fragrance Materials", 1993 published by the Allured PublishingCompany. Vanillin acetate is given F.E.M.A. No. (Flavor ExtractManufacturers Association Number) 3108; vanillin isobutyrate is givenF.E.M.A. No. 3754. Ethyl vanillin acetate however is only given C.A.S.No. 72207-94-4 at page 114 of "Flavor And Fragrance Materials", 1993,published by Allured Publishing Company.

Nothing in the prior art however discloses or infers the unobvious,unexpected organoleptic qualities of 2-ethoxy-4-formyl phenyl ester ofpropionic acid of our invention defined according to the structure:##STR7## and 2-ethoxy-4-formyl phenyl ester of propionic acid of ourinvention defined according to the structure: ##STR8## is not disclosedin the literature and is a novel material.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1A is the GC spectrum for the crude reaction product of Example Icontaining the compound having the structure: ##STR9## (Conditions: 50meter×0.32 mm carbowax 20M column programmed from 75°-250° C. at 2° C.per minute).

FIG. 1B is the GC spectrum for the crude reaction product of Example Icontaining the compound having the structure: ##STR10## (Conditions: 50meter×0.32 mm bonded methyl silicone column programmed from 75°-250° C.at 2° C. per minute).

FIG. 2 is the magnetic resonance spectrum for distillation Fraction 5 ofthe distillation of the reaction product of Example I for the compoundhaving the structure: ##STR11##

THE INVENTION

It has now been discovered that novel solid and liquid perfumecompositions, colognes and perfumed articles having rich, naturalvanilla bean, sweet aromas with dark chocolate topnotes may be providedby the use of 2-ethoxy-4-formyl phenyl ester of propionic acid of ourinvention having the structure: ##STR12##

The 2-ethoxy-4-formyl phenyl ester of propionic acid of our inventionhaving the structure: ##STR13## may be produced by first reacting ethylvanillin having the structure: ##STR14## with propionic anhydrideaccording to the reaction: ##STR15## thereby producing 2-ethoxy-4-formylphenyl ester of propionic acid of our invention having the structure:##STR16##

The mole ratio of propionic anhydride:ethyl vanillin may vary from about2.5:2 up to about 5:2 with a preferred mole ratio of propionicanhydride:ethyl vanillin of about 3:2.

The reaction temperature is preferably at reflux conditions (e.g., 129°C. at atmospheric pressure). Preferably the reaction is carried out atatmospheric pressures, however the reaction can be carried out at superatmospheric pressures, (e.g., greater than one atmosphere, that is, fromabout 1 up to about 10 atmospheres) and at temperatures greater than129° C. (e.g., 130°-180° C.).

At the end of the reaction, the reaction mass is neutralized with suchmaterials as aqueous sodium hydroxide or sodium carbonate or sodiumbicarbonate and then dried. The reaction mass is then distilled on afractionation column yielding fractions which are rich in the compoundhaving the structure: ##STR17##

The 2-ethoxy-4-formyl phenyl ester of propionic acid of our inventionhaving the structure: ##STR18## is capable of augmenting or enhancing orimparting rich, natural vanilla bean and sweet aromas with darkchocolate topnotes; and at the same time is non-discoloring in perfumecompositions (as compared with other vanillin derivatives).

The 2-ethoxy-4-formyl phenyl ester of propionic acid of our inventionand one or more auxiliary perfume ingredients including, for example,alcohols, aldehydes, ketones, nitriles, esters other than the2-ethoxy-4-formyl phenyl ester of propionic acid of our invention,cyclic esters (lactones), dialkyl ethers, alkyl alkenyl ethers,thioethers, thiols, carboxylic acids and hydrocarbons and naturalessential oils and synthetic essential oils may be so admixed so thatthe combined odors of the individual components produce a pleasant anddesired fragrance particularly and preferably in the natural citrusy ormusky area. Such perfume compositions usually contain (a) the main noteor the "bouquet" or the foundation stone of the composition; (b)modifieres which round off and accompany the main notes; (c) fixativeswhich include odorous substances which lend a particular note to theperfume throughout all stages of evaporation and substances which retardevaporation; and (d) topnotes which are usually low-boiling,fresh-smelling materials.

In perfume compositions, it is the individual components whichcontribute to their particular olfactory characteristics; however, theoverall sensory effect of the perfume composition will be at least thesum total of the effect of each of the ingredients. Thus, the2-ethoxy-4-formyl phenyl ester of propionic acid of our invention can beused to alter, modify, impart or enhance the aroma characteristics of orto a perfume composition, for example, by utilizing or moderating theol-factory reactions contributed by another ingredient in thecomposition.

The amount of 2-ethoxy-4-formyl phenyl ester of propionic acid of ourinvention which will be effective in perfume compositions as well as inperfumed articles and colognes depends on many factors, including theother ingredients, their amounts and the effects which are desired. Ithas been found that perfume compositions containing as little as 0.01%of the 2-ethoxy-4-formyl phenyl ester of propionic acid of our inventionor even less (e.g., 0.005%), can be used to impart a very natural,substantive, rich, natural vanilla bean and sweet aroma with darkchocolate topnotes to soaps, cosmetics and other products. The amountemployed can range up to 70% of the fragrance components and will dependon considerations of cost, nature of the end product, the effect desiredon the finished product and the particular fragrance sought.

The 2-ethoxy-4-formyl phenyl ester of propionic acid of our invention isuseful (taken alone or taken together with other ingredients in perfumecompositions) as (an) olfactory component(s) in detergents and soaps,space odorants and deodorants, perfumes, colognes, toilet waters, bathpreparations such as lacquers, brilliantines, pomades and shampoos;cosmetic preparations such as creams, deodorants, hand lotions and sunscreens; powders such as talcs, dusting powders, face powders andperfumed article compositions of matter such as perfumed polypropylene,polyethylene and polyurethanes, particularly long-lasting or partiallyshort-lasting mixtures of, for example, encapsulated perfumes suspendedin free perfume compositions and the like.

When used as (an) olfactory component(s), as little as 0.1% of the2-ethoxy-4-formyl phenyl ester of propionic acid of our invention willsuffice to impart an intense non-discoloring rich, natural vanilla beanand sweet aroma with dark chocolate topnotes. Generally, no more than 3%of the 2-ethoxy-4-formyl phenyl ester of propionic acid of our inventionbased on the ultimate end product is required in the perfumecomposition.

In addition, the perfume composition or fragrance composition of ourinvention can contain a vehicle or carrier for the 2-ethoxy-4-formylphenyl ester of propionic acid of our invention. The vehicle can be aliquid such as a non-toxic alcohol (e.g., ethyl alcohol), a non-toxicglycol (e.g., propylene glycol or 1,2-butylene glycol or sorbitol) orthe like. The carrier can also be an absorbent solid such as a gum(e.g., gum arabic, xanthan gum, guar gum or the like) or components forencapsulating the material (such as gelatin or ethyl cellulose as bycoacervation).

When used as a component of a perfumed article such as a perfumedplastic or solid or liquid anionic, cationic, nonionic or zwitterionicdetergent or a drier-added fabric softener article or fabric softenercomposition or a shampoo or a soap, the range of 2-ethoxy-4-formylphenyl ester of propionic acid of our invention useable varies from0.005% up to about 5% by weight of the perfumed article. The lower rangeof this range, e.g., 0.005% up to 0.1% of the 2-ethoxy-4-formyl phenylester of propionic acid of our invention is most preferred when using itin a drier-added fabric softener article or fabric softener compositionin view of the need for a "non-perfumy" but pleasant head space aromaabove the batch of clothes dried using the drier-added fabric softenerarticle or fabric softener composition in a standard automaticallyoperated tumble drier.

It will thus be apparent that the 2-ethoxy-4-formyl phenyl ester ofpropionic acid of our invention can be utilized to augment, alter andmodify or enhance sensory properties particularly organolepticproperties of a wide variety of consumable materials.

The following examples are illustrative and the invention is to beconsidered to be restricted thereto only as indicated in the appendedclaims. Example I sets forth a process for producing the2-ethoxy-4-formyl phenyl ester of propionic acid of our invention.Example II, et seq., set forth the organoleptic utilities of the2-ethoxy-4-formyl phenyl ester of propionic acid of our invention.

All parts and percentages given herein are by weight unless otherwisespecified.

EXAMPLE I Preparation of 2-ETHOXY-4-FORMYL Phenyl Ester of PropionicAcid

Reaction: ##STR19##

Into a 2 liter reaction flask equipped with stirrer, thermometer, refluxcondenser and heating mantle are placed 332 grams of ethyl vanillin (2.0moles); 300 ml toluene and 390 grams (3.0 moles) or propionic anhydride.

The reaction mass is heated to reflux (129° C.) with stirring andmaintained at reflux for a period of one hour. At the end of the onehour period, 100 grams additional propionic anhydride is added and thereaction is continued at reflux for a period of three hours withstirring. At the end of the three hour period, the reaction mass iscooled.

With stirring, the reaction mass is admixed (quenched) with 500 ml of 5%aqueous sodium hydroxide at 25° C.

The reaction mass is then washed with two volumes of water and theorganic phase is separated from the aqueous phase.

The reaction mass is then "rushed over" at 155° C. and 1 mm/Hg.pressure.

The reaction mass is then fractionally distilled yielding the followingfractions:

    ______________________________________                                                  Vapor        Liquid  Vacuum                                         Fraction  Temp.        Temp.   mm/Hg.                                         No.       (°C.) (°C.)                                                                          Pressure                                       ______________________________________                                        1         69/42        23/109  12.0/3.0                                       2          31          125     2.0                                            3         154          158     0.8                                            4         155          158     0.85                                           5         157          168     0.85                                           6         151          210     0.8.                                           ______________________________________                                    

FIGS. 1A and 1B are GC spectra for the crude reaction product prior todistillation.

FIG. 2 is the magnetic resonance spectrum for distillation Fraction 5.

The resulting product has an intense and substantive rich, naturalvanilla bean, sweet aroma with dark chocolate topnotes.

EXAMPLE II Fragrance Formulations

To demonstrate the use of the 2-ethoxy-4-formyl phenyl ester ofpropionic acid of our invention prepared according to Example I, inmagnolia, musk and citrusy formulations the following formulae areprepared:

    ______________________________________                                                          Parts by Weight                                             Ingredients         II(A)   II(B)    II(C)                                    ______________________________________                                        Phenylethyl alcohol 200     25       25                                       Geraniol            400     25       25                                       Trichloromethylphenyl                                                                             20       5        5                                       carbinyl acetate                                                              Phenylethyl acetate 60       5        5                                       Undecylenic aldehyde                                                                               5       0        0                                       (10% in diethyl phthalate)                                                    n-Nonyl aldehyde     2       0        0                                       (10% in diethyl phthalate)                                                    Musk ketone         10      150      20                                       Musk ambrette       10      150      20                                       Eugenyl phenyl acetate                                                                            20       5        5                                       Citronellol         100     100      400                                      Vanillin             6       6        6                                       (10% in diethyl phthalate)                                                    Eugenol             30       5        5                                       Citronellyl formate 30       5        5                                       Geranyl acetate     10       5        5                                       Linalool            40      20       20                                       Geranyl phenyl acetate                                                                            50      20       20                                       Cis-beta, Gamma-hexenyl acetate                                                                    2       0        0                                       1-(2,5,5-Trimethyl-1,3-cyclo-                                                                      5       5        5                                       hexadien-1-yl)-1,3-butanedione                                                Farnesene isomer mixture produced                                                                 60      60       40                                       according to Example I of U.S.                                                Letters Patent No. 4,394,444 (the                                             specification for which is                                                    incorporated by reference herein)                                             2-Ethoxy-4-formyl phenyl                                                                          120     120      120                                      ester of propionic acid                                                       having the structure:                                                          ##STR20##                                                                    produced according                                                            to Example I, supra.                                                          ______________________________________                                    

The addition of 2-ethoxy-4-formyl phenyl ester of propionic acid of ourinvention to each of the formulations of Examples II(A), II(B) and II(C)adds to these fragrances intense rich, natural vanilla bean and sweetundertones with dark chocolate topnotes.

Accordingly, the perfume composition of Example II(A) can be describedas "a magnolia aroma with rich, natural vanilla bean and sweetundertones and dark chocolate topnotes".

The perfume composition of Example II(B) can be described as "a muskaroma with rich, natural vanilla bean and sweet undertones and darkchocolate topnotes".

The perfume composition of Example II(C) can be described as "a citrusaroma having rich, natural vanilla bean and sweet undertones with darkchocolate topnotes".

Each of the perfume formulations as a result of containing the compoundhaving the structure: ##STR21## in the amount set forth, supra, and inthe concentration set forth, supra, gives rise to non-discoloringperfume formulations.

EXAMPLE III

Preparation of Soap Composition

One hundred grams of soap chips are produced according to Example V ofU.S. Pat. No. 4,058,487 issued on Nov. 15, 1977 the specification forwhich is incorporated by reference herein, as follows:

The sodium salt of an equal mixture of C₁₀ -C₁₄ alkane sulfonates (95%active), 40 pounds, is dissolved in a mixture of 80 pounds of anhydrousisopropanol and 125 pounds of dionized water at 150° F. In this mixtureis dissolved 10 pounds of partially hydrogenated coconut oil, fattyacids and 15 pounds of sodium mono-C₁₄ -alkylmaleate. The pH of thesolution is adjusted to 6.0 by the addition of a small amount of a 50%aqueous sodium hydroxide solution. The isopropanol is distilled off andthe remaining aqueous solution is drum dried. The resulting solidactives are then blended in a chip mixture with 10 pounds of water, 0.2pounds titanium hydroxide and 0.75 pounds of one of the materials setforth below:

                  TABLE I                                                         ______________________________________                                        Perfume Ingredient                                                                           Perfume Profile                                                ______________________________________                                        2-Ethoxy-4-formyl phenyl                                                                     A rich natural vanilla bean, sweet                             ester of propionic acid                                                                      aroma with dark chocolate topnotes.                            having the structure:                                                          ##STR22##                                                                    Perfume composition                                                                          A magnolia aroma with rich, natural                            of Example II(A).                                                                            vanilla bean and sweet undertones                                             and dark chocolate topnotes.                                   Perfume composition                                                                          A musk aroma with rich, natural                                of Example II(B).                                                                            vanilla bean and sweet undertones                                             and dark chocolate topnotes.                                   Perfume composition                                                                          A citrus aroma having rich, natural                            of Example II(C).                                                                            vanilla bean and sweet undertones                                             with dark chocolate topnotes.                                  ______________________________________                                    

The chips are then plodded into logs, cut to size and finally stampedinto bars, having a pH of approximately 6.9.

Each of the perfumed soaps of Table I above manifests an excellentcharacteristic aroma as indicated in Table I above. Furthermore, each ofthe perfume soaps is non-discoloring.

EXAMPLE IV Preparation of A Detergent Composition

A total of 100 grams of a detergent powder prepared according to U.S.Pat. No. 4,058,472 and containing 5% by weight of the sodium salts of amixture of sulfonated C₁₄ -C₁₈ alkyl catechol as a surface activecomponent, the mixture being 60 parts by weight of mono-C₁₄ -C₁₈ alkylcatechol and 40 parts by weight of di-C₁₄ -C₁₈ alkyl catechol, 35% ofsodium tetrapyrophosphate, 30% of sodium silicate, 20% of sodiumcarbonate, 3% of sodium carboxymethyl cellulose and 7% of starch ismixed with 0.15 grams of one of the perfume ingredients of Table I ofExample III, supra, until a substantially homogeneous composition isobtained. This composition has an excellent aroma as indicated accordingto Table I of Example III, supra.

EXAMPLE V Preparation of Cosmetic Powder Compositions

A cosmetic powder is prepared by mixing in a ball mill 100 grams oftalcum powder with 0.25 grams of one of the perfume materials of Table Iof Example III, supra. Each of the cosmetic powders has an excellentaroma as set forth in Table I of Example III, supra.

EXAMPLE VI Perfumed Liquid Detergents

Concentrated liquid detergents having aromas as set forth in Table I ofExample III, supra, are prepared by adding 0.10%, 0.15% and 0.20% ofeach of the perfume ingredients of Table I of Example III, supra. Theyare prepared by adding and homogeneously mixing the appropriate quantityof perfume material in the liquid detergent. The detergents all possessaromas as set forth in Table I of Example III, supra.

EXAMPLE VII Preparation of Cologne and Handkerchief Perfumes

Each of the compositions of Table I of Example III, supra, isincorporated into colognes at several concentrations, 2.0%, 2.5%, 3.0%,3.5%, 4.0% and 5.0% in 70%, 75%, 80%, 85% and 90% aqueous ethanol; andinto handkerchief perfumes at concentrations of 10%, 15%, 20% and 25%(in 80%, 85%, 90% and 95% aqueous ethanol). The use of each of theperfume ingredients as set forth in Table I of Example III, supra,affords distinctive aromas as set forth in Table I of Example III,supra.

EXAMPLE VIII Preparation of A Composition

A total of 100 grams of a detergent powder (a non-ionic detergent powdercontaining a proteolytic enzyme prepared according to Example I ofCanadian Patent No. 985,190 issued on Mar. 9, 1976) is mixed with 0.15grams of a perfume material set forth in Table I of Example III, supra,until a substantially homogeneous composition is obtained in each case.Each of the compositions has an excellent aroma as set forth in Table Iof Example III, supra.

EXAMPLE IX

Utilizing the procedure of Example I at column 15 of U.S. Pat. No.3,632,396 (which is hereby incorporated by reference into the instantspecification), a nonwoven cloth substrate useful as a dryer-addedfabric softening article of manufacture is prepared wherein thesubstrate, the substrate coating and the outer coating and the perfumematerial are as follows:

1. a water "dissolvable" paper ("Dissolvo Paper");

2. Adogen 448 (m.p. about 140° F.) as the substrate coating; and

3. an outer coating having the following formulation (m.p. about 150°F.):

57%--C₂₀₋₂₂ HAPS

22%--isopropyl alcohol

20%--antistatic agent

2.5%--of one of the perfume materials of Table I of Example III, supra.

A fabric softening composition prepared as set forth above having anaroma characteristic as set forth in Table I of Example III, supra,consists of a substrate having a weight of about 3 grams per 100 squareinches, a substrate coating of about 1.85 grams per 100 square inches ofsubstrate and an outer coating of about 1.4 grams per 100 square inchesof substrate, thereby providing a total aromatized substrate and anouter coating weight ratio of about 1:1 by weight of the substrate. Theresulting aromas can be described as set forth in Table I of ExampleIII, supra, and are imparted in pleasant manners to the head space inthe dryer on operation thereof using said dryer-added fabric softeningnonwoven fabric.

EXAMPLE X Perfumed Polyethylene

Scented polyethylene pellets having a pronounced aroma as set forth inTable i of Example III, supra, are prepared as follows (in accordancewith Example III of U.S. Pat. No. 3,505,432 which is incorporated byreference herein).

75 Pounds of polyethylene of a melting point of about 220° F. are heatedto about 230° F. in a container as illustrated in FIGS. 1 and 2 of U.S.Pat. No. 3,505,432. 25 Pounds of one of the perfume materials of Table Iof Example III, supra, are then quickly added to the liquifiedpolyethylene, the lid is put in place and the agitating means areactuated. The temperature is maintained at about 225° F. and the mixingis continued for about 15 minutes. The valve is then opened to allowflow of the molten polyethylene enriched with the perfume containingmaterial to exit through the orifices as indicated in FIGS. 1 and 2 ofU.S. Pat. No. 3,505,432. The liquid falling through the orificessolidifies almost instantaneously upon impact with the moving cooledconveyor. Solid polyethylene beads or pellets having a pronounced aromaas set forth in Table I of Example III, supra, are thus formed. Analysisdemonstrates that the pellets contain about 25% of the perfume substanceof Table I of Example III, supra, so that almost no losses of thescenting substance occur. These pellets may be called master pellets. 50Pounds of the perfume substance containing master pellets are then addedto 1000 pounds of unscented polyethylene powder and the mass is heatedto the liquid state. The liquid is molded into thin sheets or films. Thesheets or films have a pronounced aroma as set forth in Table I ofExample III, supra.

EXAMPLE XI Scented Polypropylene

100 Pounds of polypropylene are heated to about 300° F. 30 Pounds of oneof the aroma materials of Table I of Example III, supra, are added tothe liquified polypropylene. The procedure is carried out in theapparatus of FIGS. 1 and 2 of U.S. Pat. No. 3,505,432. After mixing forabout 8 minutes, the valve is opened to allow the exit of thepolypropylene-scented material mixture whereby solid pellets having apronounced aroma as set forth in Table I of Example III, supra, areformed on the conveyor. The pellets thus obtained are then admixed withabout 20 times their weight of unscented polypropylene and the mixtureis heated and molded into flat discs. The flat discs have a strong andpleasant aroma as set forth in Table I of Example III, supra.

EXAMPLE XII

A perfumed polymer is produced by admixing a microporous polymerproduced according to one of Examples 194-236 of U.S. Pat. No. 4,247,498(the disclosure of which is incorporated by reference herein), andapplying a 0.5 mm/Hg. vacuum to the system. The resulting product isthen compressed into pellets and molded into fragrance-emitting plasticobjects, e.g., automobile dashboards.

What is claimed is:
 1. 2-ethoxy-4-formyl phenyl ester of propionic acidhaving the structure: ##STR23##
 2. A process for augmenting or enhancingthe aroma of a consumable material selected from the group consisting ofperfume compositions, colognes and perfumed articles comprising the stepof adding to said consumable material an aroma augmenting, imparting orenhancing quantity of 2-ethoxy-4-formyl phenyl ester of propionic aciddefined according to c3laim
 1. 3. The process of claim 2 wherein theconsumable material is a perfume composition.
 4. The process of claim 2wherein the consumable material is a cologne.
 5. The process of claim 2wherein the consumable material is a perfumed article and the perfumedarticle is a solid or liquid anionic, cationic, nonionic or zwitterionicdetergent.
 6. The process of claim 2 wherein the consumable material isa perfumed article and the perfumed article is a perfumed polymer. 7.The process of claim 2 wherein the consumable material is a perfumedarticle and the perfumed article is a fabric softener composition ordrier-added fabric softener article.
 8. A perfume composition consistingessentially of a perfume base and intimately admixed therewith in aperfume imparting, augmenting or enhancing quantity or concentration2-ethoxy-4-formyl phenyl ester of propionic acid defined according toclaim
 1. 9. A solid or liquid anionic, cationic, nonionic orzwitterionic detergent composition consisting essentially of a solid orliquid anionic, cationic, nonionic or zwitterionic detergent base andintimately admixed therewith an aroma augmenting, enhancing or impartingquantity or concentration of the 2-ethoxy-4-formyl phenyl ester ofpropionic acid defined according to claim
 1. 10. A perfumed polymerconsisting essentially of a microporous polymer and containing in theinterstices thereof an aroma imparting, augmenting or enhancing quantityof the 2-ethoxy-4-formyl phenyl ester of propionic acid of claim
 1. 11.A perfumed polymer consisting essentially of a microporous polymer andcontained in the interstices thereof an aroma imparting, augmenting orenhancing quantity of the perfume composition of claim
 8. 12. A cologneconsisting essentially of water, ethanol and the 2-ethoxy-4-formylphenyl ester of propionic acid defined according to claim 1.